After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.

Jake takes out an ad in the newspaper after the suicide of his unfaithful fiancée, in an effort to understand the reasons for the betrayal. By soliciting the secret diaries of other women, he hopes to find some reconciliation with the truth.